A large suspension bridge at night with illuminated cables and a central tower.

New Windsor Vacation Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for New Windsor vacation rentals

Fireplace, books

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (14 reviews)
"The property was well maintained, it felt very cozy and well located in the town. Host were amazing as they were always present to help me with any problem I had even though I never needed them."
United States
Sebastian A.
The price is SAR 403
SAR 785 total
includes taxes & fees
8 Jul - 9 Jul
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Interior

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful place tucked back in the woods. Very relaxing and incredibly clean. The free coffee was a nice touch too. Will 100% be returning to The Gunks because of this house. "
United States
Kyle T.
The price is SAR 295
SAR 623 total
includes taxes & fees
23 Jun - 24 Jun
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Interior

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (37 reviews)
"Clean, welcoming, great location."
United States
Nicolae P.
The price is SAR 360
SAR 734 total
includes taxes & fees
2 Jul - 3 Jul
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Terrace/patio

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (9 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is SAR 469
SAR 1,460 total
includes taxes & fees
23 Jun - 24 Jun
House on the Babbling Brook- Quiet 2BR + King Bed!
Property grounds

TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (7 reviews)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
The price is SAR 513
SAR 895 total
includes taxes & fees
30 Jun - 1 Jul
TRANQUIL MOUNTAIN SOLITUDE
Property grounds

Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
8.8 out of 10, Excellent, (3 reviews)
"This is an "upgraded" camping experience! A peaceful setting for outdoor living, exceptionally private. Super convenient to Minnewaska. Everything you need amd exactly as described, plenty of seating for a larger group and sleeping tent/yurt makes inclement weather less of a concern than a regular tent or backpacking setup. Definitely stay here!"
United States
Megan
The price is SAR 321
SAR 570 total
includes taxes & fees
23 Jun - 24 Jun
Glamping Tent & Campsite by Minnewaska State Park
Terrace/patio

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is SAR 634
SAR 1,038 total
includes taxes & fees
23 Jun - 24 Jun
Cabin in the heart of the Hudson Valley, Cabin 3
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (139 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
The price is SAR 743
SAR 1,228 total
includes taxes & fees
23 Jun - 24 Jun
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Terrace/patio

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Gardiner
10.0 out of 10, Exceptional, (17 reviews)
"Amazing space, amenities and view! A perfect winter getaway. "
United States
Lee E.
The price is SAR 809
SAR 1,234 total
includes taxes & fees
6 Jul - 7 Jul
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Cottage (2 Bedrooms) | Interior

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
The price is SAR 687
SAR 1,933 total
includes taxes & fees
28 Jun - 29 Jun
Hudson Valley Retreat w/ Pool Near Greenwood Lake
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (34 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is SAR 634
SAR 1,038 total
includes taxes & fees
23 Jun - 24 Jun
Cabin in the Heart of the Hudson Valley, Cabin 1
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (68 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
The price is SAR 563
SAR 1,077 total
includes taxes & fees
23 Jun - 24 Jun
Cozy country efficiency in the Hudson Valley
Smart TV

King Bed | Private Parking | Strong WiFi

King Bed | Private Parking | Strong WiFi
Poughkeepsie
The price is SAR 339
SAR 1,302 total
includes taxes & fees
30 Jun - 1 Jul
King Bed | Private Parking | Strong WiFi
Shower, hair dryer, towels, soap

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Warwick
10.0 out of 10, Exceptional, (41 reviews)
"Absolutely ideal comfort, cleanliness, amenities that are top notch for the kitchen and bathroom and luxury at the heart of Main Street in Warwick."
United States
Melissa V.
The price is SAR 436
SAR 964 total
includes taxes & fees
23 Jun - 24 Jun
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Property grounds

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (84 reviews)
"great location and nice host"
United States
christopher s.
The price is SAR 446
SAR 882 total
includes taxes & fees
5 Jul - 6 Jul
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Smart TV

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is SAR 557
SAR 1,109 total
includes taxes & fees
5 Jul - 6 Jul
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Exterior

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (4 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is SAR 661
SAR 1,087 total
includes taxes & fees
23 Jun - 24 Jun
Historic Cabin with Pool & Fire Pit
Interior

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
9.0 out of 10, Wonderful, (16 reviews)
"The host was very helpful and considerate, the rooms was nice."
United States
David A.
The price is SAR 456
SAR 720 total
includes taxes & fees
23 Jun - 24 Jun
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Interior

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
9.6 out of 10, Exceptional, (29 reviews)
"Clean and quiet."
United States
Ted
The price is SAR 346
SAR 711 total
includes taxes & fees
21 Jul - 22 Jul
Dream getaway apartment in the foot of Gunks Ridge
Exterior

2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.8 out of 10, Exceptional, (19 reviews)
"great place tostay"
United States
Anonymous traveler
The price is SAR 413
SAR 477 total
includes taxes & fees
28 Jun - 29 Jun
2 Full Beds | Non-Smoking, Kitchen
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top New Windsor Hotel Reviews

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"Great staff"
badwin 1-night trip
Posted less than an hour ago
Sleep Inn & Suites Middletown - Goshen

Frequently asked questions

Can I find a vacation rental in New Windsor?

Yes, we have vacation rentals near the most popular local attractions in New Windsor, or you can select a secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in New Windsor. Allow lots of time to check out the lakeside and coffeehouses during your visit.

What's the top vacation rental in New Windsor?

Lakefront Paradise Pool + Paddle Boats Sleeps 12: Visitors like this New Windsor vacation home rental. It offers an outdoor pool, a balcony, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in New Windsor?

Choose from 11 Expedia vacation rentals in New Windsor for a memorable vacation.

What can I see and do in New Windsor?

Cultural attractions to visit include Knox's Headquarters State Historic Site and National Purple Heart Hall of Honor. Woodbury Common Premium Outlets and LEGOLAND® New York are other popular places to visit in the area.

What are vacation rentals like in New Windsor?

Vacation rentals are private accommodations you can stay in for a short or long stay in New Windsor. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.